Good Morning Lauren,You find yourself in a fortunate position to ease into the real estate investing space. 

I think the rental market in Westport is the key factor, however, because the ease of finding something better (and cheaper) will have a big impact on whether they will move. 

Will now be looking for private money at 2 points and 10%, simply because the ease is worth the extra interest and that's a solid return for a private money lender as well. 

Mortgage rates have already shown signs of easing.  

I've also had friends do far better in real estate, and the ease of using leverage appeals to me as well.Due to my 9-5 I have this amazing advantage when I talk to people, in that I get to vet them better than just about anyone else can, and many of the people I see who have a financial position I would like for myself are involved in real estate.So yeah, I'm at the point that every thing I read gives me 5 new questions, I getting some of the jargon down.  

There are other benefits to mitigate the paying a higher rate, like ease/certainty of close (varies with each lender of course), you can close in an LLC, less stringent requirements, closing time is usually significantly reduce in comparison with banks. 

Perhaps it has something to do with ease of lending on commercial properties but doubtful.

Might serve to ease your anxiety when the time comes to deploy that cash you've been stockpiling in the meantime.Best 

The cheapest option will normally be best but also look at things like turnaround times on draw funds, closing time, ease of use from past reviews, etc.

If one can be at ease with the negatives, specifically 1. rent court/evictions 2. maintenance 3 chasing rent money...